Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| Challenger Fairfield | 2019/10/07 22:00 | Colin Sinclair v Agustin Velotti | 7-6,6-7,4-6 |
| Challenger Tiburon | 2019/09/23 21:20 | Michail Pervolarakis v Colin Sinclair | 6-3,7-6 |
| Challenger Columbus 3 | 2019/09/17 15:40 | Colin Sinclair v Alexander Erler | 5-7,6-7 |
| Davis Cup | 2019/09/14 08:10 | Colin Sinclair v Omar Alawadhi | 7-5,3-6,6-2 |
| Davis Cup | 2019/09/13 08:05 | Colin Sinclair v Saud Alhaqbani | 6-1,6-1 |
| Davis Cup | 2019/09/11 08:05 | Colin Sinclair v Dipu Lal | 6-0,6-0 |
| Challenger New Haven | 2019/09/03 17:45 | Thai-Son Kwiatkowski v Colin Sinclair | 7-6,6-2 |
| ITF M15 Cancun | 2019/08/23 14:00 | Colin Sinclair v Thiago Agustin Tirante | 4-6,4-6 |
| ITF M25 Waco | 2019/10/15 16:55 | Connor Farren v George Goldhoff | 4-6,6-2,11-13 |
| ITF M25 Waco | 2019/10/13 15:00 | Connor Farren v Hendrik Jebens | 7-6,6-2 |
| ITF M25 Claremont | 2019/10/10 18:00 | Liam Broady v Connor Farren | 4-6,6-3,6-1 |
| ITF M25 Claremont | 2019/10/09 18:40 | Connor Farren v Jonathan Gray | 3-6,6-3,6-4 |
| ITF M25 Harlingen | 2019/09/25 16:20 | Connor Farren v Govind Nanda | 2-6,6-1,4-6 |
| ITF M25 Houston | 2019/09/20 00:00 | Connor Farren v Austin Rapp | 5-7,6-7 |
| ITF M25 Houston | 2019/09/18 23:30 | Peter Bothwell v Connor Farren | 4-6,3-6 |
| Challenger Cary | 2019/09/10 17:25 | JC Aragone v Connor Farren | 6-2,7-6 |